In the original 1968 film The Thomas Crown Affair, the song is heard – sung by Noel Harrison – during a scene in which the character Thomas Crown flies a glider at the glider airport in Salem, New Hampshire: having edited the rough cut for this scene utilizing the Beatles track "Strawberry Fields Forever" producer/ director Norman Jewison commissioned an original song be written for the glider scene which would reference the ambivalent feelings of Thomas Crown as he engages in a favorite pastime while experiencing the tension of preparing to commit a major robbery. Alan Bergman: "Michel [Legrand] played us [ie. Alan and Marilyn Bergman] seven or eight melodies. We listened to all of them and decided to wait until the next day to choose one. We three decided on the same one, a long baroque melody...The lyric we wrote was stream-of-consciousness. We felt that the song had to be a mind trip of some kind" – "The [eventual] title was [originally] a line at the end of a section...When we finished we said: "What do we call this? It's got to have a title. That line is kind of interesting.' So we restructured the song so that the line appeared again at the end. It came out of the body of the song. I think we were thinking, you know when you try to fall asleep at night and you can't turn your brain off and thoughts and memories tumble." [2]

Noel Harrison recorded the song after Andy Williams passed on it: according to Harrison: "It was recorded live on a huge sound stage at Paramount, with the accompanying film clips running on a giant screen and Michel blowing kisses to the orchestra." [3] Harrison took issue with the couplet "Like a tunnel that you follow to a tunnel of its own/ Down a hollow to a cavern where the sun has never shone", singing the word "shone" British-style with a short vowel sound making the rhyme with "own" imperfect. Marilyn Bergman: "We said 'No, it's shone [long vowel sound].' And he said 'No, it's our language!' And we said: 'Yes, but it's our song.' So reluctantly, he sang shone [long vowel sound] and our rhyme was intact." [2] However, Harrison evidently had the last laugh; in the finally released version he sings "shone" with a short vowel! Harrison's version had a US single in the US in July 1968 soon after the premiere of its parent film, and similarly was issued in the British Isles at the time of the film's 7 February 1969 premiere in the UK and Ireland, and as a result was a current UK release when "The Windmills of Your Mind" was afforded the cachet of being nominated for an Academy Award in a 24 February 1969 announcement: Harrison's single debuted in the UK Top 50 dated 4 March 1969 at #36 and had risen to #15 – abetted by performances by Harrison on the 27 March 1969 broadcast of TOTP and also on variety shows hosted by Rolf Harris and Scott Walker – when the song was announced as the Academy Award winner on 14 April 1969, an endorsement which facilitated the Top Ten entry of Harrison's single on the UK chart dated 22 April 1969 with its chart peak of #8 effected two weeks later.[4]

"The Windmills of Your Mind" was performed on the Academy Awards ceremony broadcast of 14 April 1969 by José Feliciano; Noel Harrison would recall: "I was invited to sing it at the Academy Awards... but I was making a movie in England at the time, and the producer (who didn’t like me) refused to let me go." The film which caused the scheduling conflict has been identified as Take a Girl Like You directed by Jonathan Miller.[3]

Jerry Wexler, president of Atlantic Records, heard "The Windmills of Your Mind" on the soundtrack of The Thomas Crown Affair and championed having Dusty Springfield record the song for her debut Atlantic album Dusty in Memphis, overcoming the singer's strong resistance; Springfield's friend and subsequent manager Vicki Wickham would allege: "Dusty always said she hated it because she couldn't identify with the words." [5] During the first sessions for the track at American Sound Studio in Memphis, problems with getting the proper chords down arose, and at Springfield's suggestion the song was arranged so the first three verses were sung in a slower tempo than the original film version.

In April 1969 the third A-side release from Dusty in Memphis was announced as "I Don't Want to Hear It Anymore" with "The Windmills of Your Mind" as B-side: however Wexler was prepared to promote "The Windmills..." as the A-side if it won the Oscar for Best Song, reportedly instructing mail-room clerks at Atlantic Records' NYC headquarters to listen to the Academy Awards broadcast the night of 14 April 1969; hearing "The Windmills..." announced as the Best Song winner was these clerks' cue to drive a station wagon loaded with 2500 copies of a double-sided promo single of Springfield's version – identified on the label as "Academy Award Winner" – to the NYC general post office, where the copies of the single were mailed out to key radio stations across the US.[6] Although its Hot 100 debut was not effected until the 5 May 1969 issue of Billboard and then with a #99 ranking, Springfield's "The Windmills..." made a rapid ascent to the Top 40 being ranked at #40 on the Hot 100 dated 24 May 1969 only to stall over the subsequent three weeks peaking at #31 on the Hot 100 dated 14 June 1969 with only one additional week of Hot 100 tenure, being ranked at #45 on the 21 June 1969 chart. Local hit parades indicate that Springfield's "The Windmills..." had Top Ten impact in only select larger markets: Boston, SoCal, and Miami. The track did reach #3 on the Easy Listening chart in Billboard a feat matched by Springfield's third subsequent single "Brand New Me" which therefore ties with "The Windmills..." as having afforded Springfield her best-ever solo showing on a Billboard chart.[7][8]

"The Windmills of Your Mind" was recorded by José Feliciano for his 1969 album 10 to 23,[9] and Feliciano performed the song on the Academy Awards ceremony broadcast of 14 April 1969; the song's original singer Noel Harrison would later opine of Feliciano's performance: "A wonderful musician and compelling singer, he made much too free with the beautiful melody in my humble opinion. But that's jazz." [3] It was Feliciano's version of "The Windmills..." which became a hit in the Netherlands, reaching #11 on the Dutch chart in November 1969.[10] and Nr.4 in Turkish hit parade in April 1970 [11]

Taped performance from The Jeff Graham Show on Radio Luxembourg, made in 1989: the track was included on some editions of the 1989 single release "When in the World", and is also included on the 2014 compilation The Essential Swing Out Sister

The lyrics for the French-language rendering of "The Windmills of Your Mind" were written by Eddy Marnay and this version, entitled "Les Moulins de mon Cœur", was first recorded in 1968 by Marcel Amont who was resultantly afforded a minor French chart hit (peak #49).[90]

In 1970 Helena Vondráčková, prior to recording "The Windmills of Your Mind" with its original English lyrics for her album Isle of Helena (1972), recorded the song as rendered in Czech: "Můžeš zůstat, můžeš jít",[113] and also Japanese: "Kaze no sasayaki".[114] Introduced on the album "Ostrov Heleny Vondráčkové",[113] "Můžeš zůstat, můžeš jít" has become a signature song for Vondráčková: in 2012 when her three CD retrospective (Nejen) o lásce was issued, Vondráčková cited "Můžeš zůstat, můžeš jít" as "the song on the [anthology] dearest to [her] heart".[115] An alternate Czech rendering of "The Windmills of Your Mind": "Mlýnské kolo v srdci mém", was recorded by Hana Hegerová to serve as title cut for her 2010 album of renderings of famous French-language songs.[116]